4-Toluenesulfonyl chloride → HCID 86608764、化合物

HRID 57287ノート

反応式

HRID 57287 の反応式
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:23])=[C:11]([C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[C:12]#[N:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[S:31](Cl)([C:34]1[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=1)(=[O:33])=[O:32]>ClCCl>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]([O:23][S:31]([C:34]2[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=2)(=[O:33])=[O:32])=[C:11]([C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[C:12]#[N:13])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1363358063-(1-Acetylpiperidin-4-yl)-2-benzothiazol-2-yl-3-hydroxyacrylonitrile

生成物 1

HCID 86608764HCID 86608764、化合物収率 23%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of the above prepared 3-(1-acetylpiperidin-4-yl)-2-benzothiazol-2-yl-3-hydroxyacrylonitrile (415 mg, 1.27 mmol) in anhydrous dichloromethane (20 mL) at room temperature under argon were added triethylamine (193 mg, 1.9 mmol) and tosyl chloride (303 mg, 1.59 mmol) in small portions. The resulting mixture was stirred at room temperature for 6 hrs. The reaction mixture was diluted with dichloromethane. The organic phase was washed with 1% HCl, 0.5% NaOH, water, brine, and dried over anhydrous sodium sulfate, filtered, and evaporated. The resulting crude product was purified by flash column chromatography eluting with CH2Cl2:MeOH=20:1 to yield 140 mg (23%) of toluene-4-sulfonic acid 1-(1-acetylpiperidin-4-yl)-2-benzothiazol-2-yl-2-cyanovinyl ester. MS (m/z, ES+): 482.1 (M+1, 100%).

後処理

  1. washThe organic phase was washed with 1% HCl, 0.5% NaOH, water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting crude product was purified by flash column chromatography
  6. washeluting with CH2Cl2

出典と根拠

ORDレコード
ord-5591322e15d04e86bb5fb719fd6f5ca4
出典データセット
uspto-grants-2016_09
特許番号
US09434720B2

反応ノート

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